Plus One
by Hypnotoad76
Summary: Jeff attends a out of town wedding with Annie. Reviews Are Welcome
1. Chapter 1

I in no way own Community. I'm just a huge fan.

As Jeff drove from the airport to the hotel he wondered why he had agreed to do this. He knew Annie could convince him to do things he'd never normally do, but talking him into going to an out of town wedding was beyond impressive. He doubted his mother would even be able to do that.

As he drove he mentally replayed the phone conversation from two days ago.

_Jeff: You want me to go with you to a wedding? In Chicago?_

_Annie: It's just for the weekend. And it won't cost you much. The bride's paying for travel expenses and the hotel rooms for everyone. And I already had a plus one so you'd be covered. It will be like a free vacation. It should be fun. _

_Jeff: The tone in your voice suggests otherwise. _

_Annie: Please Jeff. I really don't want to go by myself. Britta was suppose to go with me but-_

_Jeff: You convinced Britta to go? How drunk was she when she agreed to that? _

_Annie: I told her some people from Greenpeace would be there and that she and I could make fun of the institute of marriage. _

_Jeff: Let me guess, none of that was true. _

_Annie: Well…._

_Jeff: You're good. Wait, isn't Britta still in South America for the summer? _

_Annie: Hence the problem. She promised she'd be in Chicago by Friday morning for the wedding. I told her she should get back sooner, but no, she kept saying she wanted to stay as long as possible to get the 'whole experience'. Then a hurricane came and destroyed the airport and now she's not sure she can even get back for the beginning of classes, much less for Friday's wedding. _

_Jeff: Typical. _

_Annie: So Britta's not available. Troy and Abed have tickets for a sci-fi convention this weekend. Both Andre and Ben are sick so Shirley has to take care of them. And Pierce…..I've only talked to him once since paintball and that didn't go well so I can't ask him. _

_Jeff: I'm actually offended. You would ask Pierce to go with you before me? _

_Annie: Don't let it go to your head, but yes I would ask you to go before Pierce. I'm just letting you know that if you say no I have no one else to ask. _

_Jeff: If it's such a hassle why are you even going anyway? _

_Annie: The bride's from my rehab group. She said it's very important that everyone from our group be there for her special day. It means a lot to her. She'll never forgive me if I don't go._

_Jeff: First of all, speaking as someone who's known a lot of divorce lawyers, I doubt this will be her only 'special day'. And second, you said you never speak to anyone from rehab. And now you're scrambling to see everyone at a wedding? _

_Annie: Jeff, I'm asking you as a friend to please go with me to this wedding. _

_Jeff: Wow, I can actually see your formidable face over the phone. _

_Annie: If you do this for me I'll help you with all your homework for next year. _

_Jeff: You already do that. _

_Annie: Jeff-_

_Jeff: Ok, I'll go._

_Annie: You will! Thankyou, thankyou, thankyou!_

_Jeff: But you definitely owe me for this._

_Annie: Oh. Ok. What did you have in mind? _

_Jeff: I'm not sure yet, I'll have to think about it. It'll definitely be humiliating, but I promise it won't be cruel. _

_Annie: Ok. Wait, it's not going to have to do with living in the moment, is it? _

_Jeff: I'll see you at the wedding. _

Although he'd never admit it out loud, a part of him was actually looking forward to this. Not the wedding specifically, but spending some time with Annie. Unlike last summer he saw more of the study group during this summer. He had hung out a lot with Abed and Troy and even had dinner at Shirley's a few times. And just before she left he and Britta had had a memorable night at a karaoke bar which ended with the two of them drunkenly singing 'Piano Man' at the top of their lungs. But he had only seen Annie a couple of times. Not because he was avoiding her. It was just that with her summer job no one from the group had seen a lot of her. So being able to see her for a few days was something he could look forward to.

Though that was before she had called him yesterday to give him a detailed travel itinerary and hotel details and he found out that they would be sharing a room. It's no big deal, she had said. The room has two beds so there shouldn't be a problem. But the idea of sharing a bedroom with Annie for two nights made him more nervous than he thought it would. Seeing her was one thing, but sleeping in the same bedroom as her was something else entirely.

That information had caused him to remember a brief conversation Abed had had with him the day the two of them and Troy went to see the new Transformers movie. It was after the movie when they went to have lunch at a diner. Troy had gone to try his luck at the claw machine when out of the blue Abed said "Annie wasn't really kissing me."

Jeff looked up from his phone in shock at the change in topic. "What".

"In the library during the paintball game. When we kissed Annie wasn't really kissing me, she was kissing Han Solo. So you shouldn't be jealous of me."

"Why would I be jealous?"

"You were jealous of Rich. I just didn't want you to be jealous of me."

That was the only time they had talked about what happened between Abed and Annie during paintball (even though Abed did most of the talking.) But Jeff seemed to guess what Abed was saying; he wasn't into Annie like that so Jeff shouldn't be worried about it.

Hearing Abed say that seemed to bring up everything he felt about Annie, and how unresolved the whole situation was. That conversation, along with the sleeping arrangements, almost had him cancel this whole trip. But he knew she would never forgive him if he canceled now. So he just told himself he had to suck it up, go anyway, and find a hot single bridesmaid who had her own room.

As he pulled into the hotel parking lot he checked his watch. Originally he was supposed to fly with Annie and get in at 1:30. But his alarm clock failed to go off and he missed his flight, causing him to take the next one two hours later. He must have left a dozen messages on Annie's phone assuring her that he would be there (he knew she had to be freaking out). As he walked into the hotel and up to the front desk he quickly texted her that he was in the lobby and would be up in a few minutes.

"Hello, I'm here to check in."

The hotel clerk kept looking at the computer screen, clearly bored by his job. "Name?"

"Jeff Winger. "

"Winger, Winger." He looked up and he face lit up in sudden understanding. "OH, of course. You're here for the Statia/ Johnson wedding. I'm sorry, I should have known. A young woman named Annie Edison checked in earlier and specifically said a man named Jeff Winger would be here to check into the same room as her. She even left me a picture so I would immediately know who you were. Your girlfriend is very nice, even if she's a bit high strung."

"Oh no, we're not-"

"There you go, you're all checked in. Here's your room key, along with the photo Miss Edison left. You two make a lovely couple. Have a nice stay."

Jeff silently took the photo and looked at it. It was from Abed's birthday. He and Annie were outside the restaurant still in their Pulp Fiction costumes, but Annie had removed her wig and her hair was sticking out all over the place. He didn't tell her at the time, but he thought it made her look cute. As he looked at the photo he wondered if she had brought it to give to the hotel clerk, or if she always carried a picture of the two of them around.

He took the elevator to the fifth floor and went over to their room. He didn't want to accidently walk in on her if she wasn't decent, so he loudly knocked on the door. "Annie, its Jeff."

The door opened and there stood Annie. She had a bathrobe tightly tied around her and her hair was up in a towel turban. "Jeff! You're here." He barely had time to brace himself before she wrapped her arms around him in a tight hug. "Thank you again for doing this." She held him for a few moments before separating and dragging him into the room. "Come on, you have to get ready. Get your suit and shower stuff and get going."

"Annie, I just got here. Give me a minute before-"

"Jeff, The wedding starts at six, and it's going to take you at least an hour to get ready. I'm sure your hair alone will take a good chunk of that time."

"As I've said before." Jeff said as he pointed to his hair. "This masterpiece takes work."

"Well then get going." She said as she shoved him towards the bathroom.

"Ok, just let me get my stuff." Jeff got his suit and toiletry bag, which rivaled Shirley's purse in size, and headed into the bathroom.

An hour later he emerged all ready. He was wearing his Pulp Fiction suit, except this time he had on a red dress shirt instead of a white one. "I'm ready. So stop worrying about-"

He stopped talking and just stood there when he saw Annie. She was wearing a strapless royal blue cocktail dress. It was short enough to show off her legs, but in no way did it make her look trashy. Her hair was pinned up and she had on black high heeled shoes with straps that went around her ankles. She looked sexy and sophisticated and in every way a woman.

Annie turned around from the mirror, blushing when he kept staring at her. "What? Is there something wrong?"

"No. Nothing's wrong. I've just never- you look great."

"Thanks. So do you."

They stood there for a few moments, taking in each other's appearance, when she suddenly gasped. "Oh, I have something for you. Close your eyes."

Jeff closed his eyes, and a few moments later felt something square and medal thrust into his hands. "Ok, open them." When he opened his eyes he saw that he was holding a silver flask with a purple bow tied around it.

"Um, thank you. What's this for?"

"So you can have a good time. There's no alcohol being served no one who can't drink is tempted. And I knew this would be hard enough for you so I found a way for you to still have a few drinks so you could enjoy yourself. There's a liquor store on the way to the church, you can stop there and fill up."

Jeff looked at the flask, clearly touched by her thoughtfulness. "Thanks."

"Just promise me that you won't let anyone else drink, that you be discrete about it, that you leave any liquor bottles you buy in the car, and that you don't get too drunk."

Jeff smirked as he removed the bow. "I didn't know my present had so many rules attached to it."

"I'm serious Jeff."

"Annie, I promise I will follow each of your rules to the letter. And, this means a lot to me. Not so much that I can drink, although that's a big plus. But that you would go so out of your way for me."

He walked over and held out his arm. "Ready, Milady?

She smiled as she linked her arm with hers. "I am, Milord."


	2. Chapter 2

"Spring roll sir?"

Jeff looked down at the plate of picked at hors d'oeuvres. "I'm good. Thanks."

As the waiter walked away Jeff looked around the ballroom. It all seemed so strange. Who ever heard of a cocktail hour without any liquor? To him it seemed to bring more attention to the fact that most of the people here couldn't drink.

Though he had to admit things hadn't been that bad so far. After stopping at a liquor store so Jeff could get a bottle of rum (while Jeff usually drank scotch he figured he could covertly add it to coke and no one would know the difference) they got to the church with plenty of time to spare. Annie warmly greeted everyone from her group and introduced them to Jeff. As soon as they saw him Jeff quickly assured everyone that he wasn't Annie's boyfriend and that they were just good friends. Although she wholeheartedly agreed Jeff could have sworn he saw an unreadable look pass through her eyes at the quickness he displayed at assuring everyone that their relationship was strictly platonic.

The ceremony went very well. It wasn't too long and it was more personal then religiously ceremonial. When it was time for the bride and groom to exchange vows he heard a sniff and saw that Annie had tears running down her cheeks. Without even thinking about it Jeff took her hand and intertwined his fingers with hers. After a moment he internally started panicking about how she would react to this. But all she did was gently squeeze his hand back. They ended up holding hands for the rest of the ceremony.

The most memorable part of the whole ceremony was when it was time for the bride and groom to kiss. It just kept going, to the point where the priest was making 'wrap it up' motions with his hands. After a few moments Annie started giggling and before he could stop himself the two of them were doing everything possible to keep from hysterically laughing out loud. An older woman in front of them, who was already shocked by the length of the kiss, looked at them and said in a shrill voice "you shouldn't be laughing in the house of the Lord." This caused them to completely lose it and they had to run out of the church as their laughter echoed all around them. As they left Jeff glanced up at the alter, thinking the bride and groom would be angry at them. But no, they were using Jeff and Annie's distraction to deepen their kiss.

After the ceremony they drove back to the hotel, where the reception was being held. They joined the rest of the guests and made the rounds, introducing themselves to everyone. True to his word Jeff was being extremely discrete about adding rum to his glasses of coke. He was only on his second drink and he told himself he would only have a few more throughout the night.

"Well hello there."

Jeff turned around and saw a tall red haired woman in a tight pink dress walking towards him. "I'm Crystal."

"Jeff."

She looked him up and down, taking great pride in sizing him up. "I saw you run out of the church before laughing. I love it when people don't have the typical responses at weddings. Everyone is always so 'oh, it's so beautiful, let me sob a bunch of tears'. It's pathetic. Especially when you know they're most likely going to end up signing divorce papers."

Jeff stood there staring at her. He thought he was cynical, but this woman made him seem downright chipper. "If you hate weddings then why did you come?"

"The groom's my cousin, so I was kind of obligated. Sides, I figured I could meet a cute guy. Which from my angle that mission was accomplished. You came by yourself?"

Jeff glanced over at Annie, who was talking to two women and a man. He looked back at Crystal, who simply shrugged. "Doesn't matter. I'm sure no one will miss you for a hour or so. There's a supply closet next to the bathrooms in the lobby. Meet me there in five minutes." With that she turned and walked off, making a show of swaying her hips as she left.

Jeff downed the rest of his drink as he watched her leave. She may by unpleasant, but she was definitely hot. He was about to go join her when he looked back at Annie. She and the other two women were laughing as the guy seemed to mime climbing a ladder. As Jeff looked at them he found he didn't feel like leaving.

What are you doing, he thought. A hot angry redhead in a tight dress is waiting to have sex with you in a closet and you're not running after her? But even as he thought this he found his legs almost automatically walking over to Annie.

Annie smiled as he approached her. "Jeff, hi. Jeremy was just telling us about saving a kitten that was stuck in a tree."

"Cat saving? Isn't that usually reserved for firemen?"

Jeremy smiled ruefully. "Well yes, but that's not all I do. I also put out fires and save people from building buildings. But I have no issues with saving a cat, even though most times the reward is being scratched at."

Just then a bell rang, signaling that it was time for dinner. As everyone walked into the dining room Jeff held out his arm. Annie smiled and took it as they went over to their table.

….

"The chicken wasn't that dry."

"Are you kidding me Annie? I was about ready to dip it in my water glass so I could choke it down."

It was after dinner and everyone was out on the dance floor. Annie and Jeff had already danced through four songs. He had removed his jacket and loosened his collar, while she had lost a couple bobby pins from all the movement they were doing.

"Well at least the salad was good."

"Ok, I will give you that."

Just then the tempo changed as a slow song came on. Annie and Jeff looked at each other, smiling nervously. They moved their arms awkwardly before Jeff gently wrapped one arm around Annie's waist while taking hold of her hand with his other. Taking the lead he steered her in a tight circle, being careful not to step on her toes. As she rested her head on his chest he hoped she didn't notice that his heart was beating wildly against his ribcage. He could talk a jury into getting a drunk driver off without breaking a sweat, but being so close to this little woman was terrifying him.

When the song ended he pulled himself away from her. "I think I have to get a 'special' soda if I'm going to keep dancing. I'll be back in a sec."

Annie smiled and did a curtsey, or as much of one she could do in her dress. "Hurry back soon."

Jeff smiled as he did a small bow. "Will do, Milady."

Jeff got a soda and walked a little ways away, adding some rum to his coke. As he capped his flask he felt someone tapping on his shoulder. "I told you I'd be back in a-"

As he turned around he felt someone pull the flask out of his hand. He saw that the woman in front of him wasn't Annie, but Crystal. She held the flask in her hands as she looked at him angrily. "Well well well, look who decided to leave me waiting in a closet. And what's this here? You holding out on me?"

"Yes, that's exactly what I'm doing." Jeff tried to get the flask back but Crystal held it far behind her. "What are you, five. Just give it back to me."

"Now why would I do that? I think the bride and groom would very much like to hear that some guy is getting smashed in a room full of addicts. Or maybe I should go tell your little friend, that child who's trying to dress like a grownup. Seriously, is she your daughter or does she just have daddy issues?"

Jeff tried not to lose his cool as he looked at her smirking face. "I'd say she's a woman with more class and a better fashion sense then your bitter self will ever have. Seriously, a pink dress with red hair. Even for a straight guy I know that looks horrible. "

The smirk vanished from her face as quickly as a light bulb being turned off. She looked like she was going to throw the flask at his head. But instead she shoved it into his hands before marching off onto the dance floor.

Jeff glanced down at his reflection in the flask as the realization of what she said took hold. He was too old to ever have anything happen between himself and Annie. She was just starting her life, where he would be lucky if he could regain his before he hit 40. Anywhere they went people would look at them and whisper, thinking he was either a dirty old man or there was something seriously wrong with her. She's already been through enough hardship; he didn't need to add anymore.

Jeff uncapped the flask and drained the rest of the booze. Once it was empty he walked out of the hotel and over to his car so he could refill. Right now he didn't want to have a front row seat to his thoughts. And, maybe getting drunk would convince Annie he really was no good for her.

….

It was after midnight when their hotel room door swung open, revealing Annie supporting a very smashed Jeff. Despite him being bigger then her she managed to get him into the room and put him on one of the beds.

"So when I said not to get to drunk you heard 'hey, I'll drink a whole bottle of rum'."

"Compared to that night with Abed this was a night light. Least, least I didn't drunk dial anyone."

Annie glared at him as she sat on the other bed and removed her shoes. "My feet are killing me."

Jeff tried to remove his own shoes but realized they were already off his feet. "Where's my shoes?"

"You took them off when you decided to do the electric slide. While 'Don't Stop Believing' was playing." She finally softened at the memory of Jeff sliding around the dance floor. "Britta is going to hate me when she finds out I didn't take pictures of that."

Jeff hanged his head as he rubbed his temples. "I'm sorry Annie."

"It's not that big a deal. You did in a way become the life of the party."

"But you asked me not to drinks too much."

Annie simply shrugged. "It's ok. I've kind of grown accustomed to you doing whatever you want. That what makes you Jeff Winger."

"If I did whatever I want I wouldn't feel so guilty about the things I want to do with you."

Annie's hands paused in the middle of taking off her earrings as she looked at Jeff. Did he just say what she thought she heard? "What."

"Forget it."

She got up and sat down next to him. "Jeff, what were you trying to say?" She reached down and lifted his head up. "You can tell me."

Jeff looked into those big doe eyes of hers before leaning forward and kissing her. Her eyes widened in shock for a moment before she closed them and kissed him back. Annie wrapped her bare arms around his neck as Jeff ran his down her sides. Their tongues danced in each other's mouths as they went at it like two hormonal teenagers.

They spent the next several minutes making out before she finally pulled away from him. They both looked each other, neither sure how to proceed. "Um, I'll be right back." Annie said as she scrambled off the bed and quickly locked herself in the bathroom.

Is this really happening, she thought as she leaned against the door and slid to the floor. Are we making out? Are you making out with Jeff Winger?

She suddenly felt a surge of anger hit her. Why are you doing this to yourself? He's just going to say he didn't mean it, that you're too young, that relationships are complicated. You don't deserve this. You don't deserve to be played with like this. Because every time you think something might happen and it doesn't, it kills you inside.

She pulled herself up and walked out of the bathroom, only to see that Jeff had fallen asleep. Sighing deeply she tugged off his tie and pulled the covers over him before she changed into her sleep clothes and got into her own bed. Annie glanced over at Jeff's sleeping face before turning off the light.


	3. Chapter 3

Jeff groaned as he opened his stinging eyes. While he was hung over, he wasn't in nearly as bad of shape as he expected to be. As he looked down and saw that he had slept in his suit he thought back to what happened after he started drinking like it was his job. He remembered dancing like an idiot and at one point telling one of the groomsmen that he looked like James Bond if he was from Milwaukee (he wasn't sure what that meant.) Once the reception ended he and Annie came back to their room, and then-.

"Morning."

Jeff sat up as Annie approached him. Her hair was up in a ponytail and she had on sweatpants and a Greendale t-shirt. He was amazed she could look this good first thing in the morning. He tried to keep his face blank as the memory of kissing her (again) fully formed in his head.

"Hey. How'd you sleep?"

"Pretty good. I just got up a few minutes ago. What about you?"

"I slept fine."

Annie nodded as she sat down on the end of Jeff's bed. She took a deep breath as Jeff absentmindedly tried to comb his hair with his fingers. "Jeff, I've done a lot of thinking about what happened last night. And, before you say or do anything there's two things I have to ask you. And I need you to answer them. Ok?"

Jeff simply nodded as he looked into her eyes. "All right."

"Ok, the first thing. Us kissing last night. Was that? I mean, I know you had a lot to drink. And when you're drunk you do things you wouldn't normally do. What I need to know is, was that….I mean, if you weren't drunk. What I'm trying to say is, was that the only reason you…..?"

Jeff knew what she was asking. Was kissing her just a result of being drunk, or did it mean something more. He knew he could easily lie and say it was just him being drunk and wanting to kiss any girl, or that he didn't even remember it happening. But he knew he owed her the truth, even if it was sure to further complicate things between then. "Annie, I don't need to be drunk to want to kiss you."

Her face lit up for the briefest of moments before the smile left her face. She looked back at him with such seriousness it made her normal formidable face seem almost comical. "Ok, now the second thing. And please don't say anything until I'm finished. I've thought about this a lot and I know how this is going to sound, but you have to make a decision, regarding us, right now. Because I can't do this anymore. The false starts and condescending actions. You kiss me and then want to act like it never happened. You refuse to be with me, but freak out when I want to date other guys. Every time I think I'm over you you open that door again, and I die a little bit when you slam it shut. I need to know once and for all if you want to be with me or not. And I need to make it very clear that this is it. What I mean is, if you say you don't want to be with me then there is no second chance. If next month or so you become jealous if I'm with someone else or say that you like me and are ready to be with me it won't matter. I won't let you open that door again if you decide to close it this time. I'm not trying to influence your decision, but you need to understand what I'm saying if that's what you choose."

Annie stood up, running her sweaty palms over her pant legs. "Ok, I'm going to go have breakfast in the lobby and then say goodbye to Jill and Tom before they leave for their honeymoon. I'll be back here in about two hours." And with that she quickly left the room before he could say anything to her.

Jeff sat further up in bed, staring at the wall in shock. He realized what she really meant by saying when she would be back. It meant that was when she was expecting his answer. He essentially had two hours to tell her his decision.

He felt himself growing angry as he thought about it. Jeff Winger didn't do ultimatums. He didn't jump when someone said you have to do this or else. And who was Annie to demand anything from him. It's not like she's so great. She was annoying and high strung. She was childish and was always making him do things be would never do. Like go out of his way for others. And make him want to be a better person because she expected the best in others. Annie was kind, and sweet, and was definitely his equal. He was always on his toes when he was around her. She was attractive and made him laugh and- damn it.

Who was Jeff kidding? He was crazy about her. And as much as he hated to admit it she was right. Whether he always meant to or not he had toyed with her heart way to many times. It was time once and for all to make a decision. Could he be in a relationship with Annie Edison or not.

And that was one thing he knew to be true. A relationship. While she was incredibly hot and he would definitely like to sleep with her, he didn't want her to just be another notch on his figurative bedpost. If he was going to be with her it wouldn't just be for a quickie in a broom closet. It would be a full on relationship. Maybe that's what scared him about this whole thing.

He definitely liked her. She amused him and made him feel things he didn't think he was capable of feeling. She could make him both happy and nervous with just a simple look. If there was a one, and he never thought about one's when it came to women, she was as close as you can get.

So why was he not with her?

There were two big reasons for that; the group and her age. And now Jeff had to work out if he could get past those obstacles.

First he figured he'd deal with the problem of the group. Because while he rarely admitted it, he deeply cared about them and had to consider their feelings on this issue. Abed wouldn't care. If anything he'd see it as a plot point in the 'television show' he saw their lives as. Troy might object at first, only for fear of what dating within the group might do to all of them. But if he accepted him and Britta hooking up he'd support him dating Annie. Pierce (even though he left the group Jeff couldn't help including his reaction in all this) would simply make a few sex jokes and then go back to calling Jeff gay.

Shirley would be a harder sell. She was sure to condemn him for being in a relationship with a much younger woman and would feel he would corrupt and hurt Annie. But he was sure he could get her to come around. If it came to it he could always point out that people objected to her getting back with Andre and that worked out when she followed her heart.

Britta would be the one who would take it the hardest. Even though they were pretty much done with all that (they decided they shouldn't sleep together anymore that night they went to the karaoke bar) she would still be mad that another guy chose Annie over her. She was sure to call him a jerk and try to guilt Annie with some talk about friends not going after men the other was involved with. But he knew he could break through to her. It wouldn't be easy, but he knew Britta well enough to get her to see that this was a good thing.

So the first obstacle was thought out and dealt with. Now came the second one, the age thing. Could they put their age difference between them? To her it wasn't a concern (it never had been). But he knew people would whisper that she was a gold digger or he was either her father or a dirty old man. Could he handle others judging him when he held her hand or kissed her in public? Could he truly feel right about having a woman so young in his arms?

Jeff sighed deeply and thought about it. When it came down to it what others thought didn't affect him as much as it once did (two years at Greendale had definitely toughened him up to dealing with other people's ridicule.) And he knew it didn't affect Annie. So the final question was, did it affect him?

He thought back to other women younger than him that he had been with. Pierce's step daughter hadn't been that much older than Annie. When you really thought about it Vaughn and especially Rich weren't much younger than him. And Annie wasn't as innocent as she had been when they first met. She was living above a 'marital aid store' (he loved that that was what she called a sex shop). And he couldn't forget how vivid her dungeon & dragons sex pantomime was if he tried. She was supporting herself and was living on her own. While she still had that youthful spark of naivety, she wasn't exactly a kid anymore.

Jeff thought about the things in his life he truly regretted. And he realized that this, not being with Annie, would be something he would always regret. Because she had meant what she said. If he said no this time there wouldn't be a second chance. Even if it didn't work out he would always hate himself if he let her slip away because of fear.

Quickly throwing on his shoes Jeff grabbed a room key and left the room, taking the stairs to the lobby. When he got there he saw Annie standing next to the front doors. She had a suitcase in her hands as she walked out of the hotel.

"Annie, wait." Jeff yelled as he ran out of the hotel. Annie turned around in surprise as she handed the suitcase to Tom. Jeff stood there cursing himself for his stupidity. She wasn't leaving; she was just helping the bride and groom pack their stuff in their car.

He stood to the side as he watched her hug the couple and wish them a happy honeymoon. Once they drove away she walked over to Jeff. "I didn't expect to see you down here."

"Annie, after what you told me I've done a lot of thinking. And I have to say something to you. There are a million reasons why we shouldn't be together. Our age difference, the group, your ability to drive me crazy."

Annie's eyes started to tear as emotional pain flowed through her. But before she could say anything Jeff cupped her face in his hands and kissed her deeply. As he pulled away she looked into his eyes and almost had a heart attack from the shift in emotion her heart just felt. "Wait, are you-?

"I'm saying that none of that matters. You are one of the kindest, most wonderful women I have ever met. And if I let you go I would hate myself forever. I'm saying I'm ready to give this a chance. Annie, I can't promise you how this will end. But I'm finally ready for this to begin. "

She let out a squeal of delight as she kissed him back, practically melting from the feel of his lips. They stood there in the entranceway kissing and holding each other until she finally pulled away from him.

"I bet you say that to all the girls." She said with a grin.

Jeff smiled back. "For once Annie Edison, you are completely wrong."


	4. Epilogue

**23 months later**

"Oh, it says here that every fifteen minutes the faces protected on Crown Fountain spit water at people. And that when it was being built there was controversy that its size would cause other parks to build competing structures so-"

Jeff good naturally rolled his eyes as he pulled Annie into a one armed hug. "Annie, if you keep your head in a book reading about the sights you won't be able to see then." He said as he kissed her.

"I just think it's interesting to know more about what we're seeing. It makes you appreciate it more."

Jeff lightly bopped her on her nose. "I think we both know what I appreciate."

Annie laughed at his comment. "When did you become so lame Mr. Winger?"

"I don't know. Maybe it was when I gave you a key with a big purple bow tied to it. Or that time I didn't play laser tag with Troy, Abed and Britta because I had to get you cold medicine when you had the flu."

"I thought you said you loved it that they came with you and Troy and Abed starting doing a radio production of Star Wars on the PA system?"

"Yea, we had fun. But it was still lame that we had to cancel."

Annie chuckled and looked over as they walked by the cloud gate structure, nicknamed The Bean. They walked over and asked another tourist to take a picture of them by it. Once he gave them their camera back they looked back at the picture, showing the two of them beaming with happiness.

It had been almost two years since they started going out, and Jeff did not regret his decision at all. Once they got back to Greendale they told the group that they were now a couple. His predictions of their reactions had been fairly accurate. While he knew it wouldn't bother Abed Jeff hadn't expected that he would be their biggest supporter. Abed had brought up that "many times the two people on sitcoms no one expects to be involved romantically end up having the strongest relationship. Like Chandler and Monica on Friends." Troy had been surprised, but didn't think it was that big of a deal. Pierce (who ended up rejoining the group during the Dean's memorable attempt to bring Spain's "running of the bulls" to Greendale) had a bit of an unexpected reaction. While he made a few jokes that Jeff was just using Annie to cover up his gayness he privately pulled Jeff aside and said that he would make Jeff sorry if he ever hurt Annie.

At first Shirley poured the mother guilt on the two of them. She felt Annie was too young for Jeff and that he was just using her for "acts the bible doesn't condone." But Annie had fiercely stood up for them, saying that she wasn't a kid and that she and Jeff were extremely happy together. Perhaps it was her passion that did it because afterwards Shirley quieted down on the issue and eventually accepted them.

As predicted Britta did take the news the hardest, and was the one who took more than a day to come to terms with it. That had been a hard week. But the two of them separately had a long conversation with her about it. And she finally was happy for the two of them. When they eventually said "I love you" for the first time in front of the group she had the loudest "OH!" of everyone. Then they all groaned when she followed up with telling them that saying I Love You too often desensitizes the meaning of the phrase and turns it into just a robotic phrase couples feel they automatically have to say to each other.

It seemed Jeff was constantly finding out more reasons to love Annie. Like discovering that she occasionally talked in her sleep about back to school sales no matter what time of year it was. Or when they moved in together and he found out she had a stuffed dog named Mr. Barky Bark.

Their relationship was far from picture perfect. They argued and fought, particularly when they first started going out. One really bad fight had him spending the day with Troy, Abed and Pierce and her with Shirley and Britta to try and calm down before they apologized and made up that night. But he wouldn't change a thing about them. In some ways he was actually glad for those early fierce fights. It had proved to them that they could survive anything.

Annie smiled as she looked up at the Chicago skyline. "I love it here."

Jeff nodded in agreement. After graduation they talked about taking a vacation somewhere. And it seemed only natural that they go back to the city they started their whole relationship in. Though what Annie didn't know was that Jeff had another reason for wanting to come back here.

Making sure Annie wasn't looking he checked his pocket to make sure the ring box was still safely there. He had bought it just before they left and had been waiting for just the right place to propose. Though when he woke up today he realized he knew the perfect place.

"Come on, this way."

"But Jeff, the restaurant's in the other direction."

"There's something I want to show you first."

They started walking down Columbus Drive, in the direction of the hotel they stayed at two years ago was. It seemed only fitting that the outside lobby be the place Jeff would propose to Annie. After all, that was where they had begun this wonderful journey together.


End file.
